Chiral Aldehydes by Ring Contraction of Pento- and Hexopyranoside Epoxides
(1990) In Journal of Organic Chemistry 55(20). p.5467-5476- Abstract
The chiral aldehydes (-)-(2S,5S)- and (-)-(2S,5R)-2-[[[dimethyl( 1,1,2-trimethylpropyl)silyl]oxy]methyl]-5-methoxy-2,5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15% yield, respectively, by lithium bromide induced rearrangement of 6-O-silylated methyl 2,3- and 3,4-anhydro-a- and -d-D-hexopyranosides, obtained in two steps from methyl α- and β-D-glucopyranoside. Rearrangement of various other pento- and hexoside epoxides permitted the suggestion of probable reaction routes. Hydrogenation of the unsaturated aldehydes gave the corresponding saturated aldehydes in good yield.
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https://lup.lub.lu.se/record/d0d052f2-a53e-41e4-b2be-5aca5ac79638
- author
- Rehnberg, Nicola LU and Magnusson, Göran LU
- organization
- publishing date
- 1990-09
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of Organic Chemistry
- volume
- 55
- issue
- 20
- pages
- 10 pages
- publisher
- The American Chemical Society (ACS)
- external identifiers
-
- scopus:0001263595
- ISSN
- 0022-3263
- DOI
- 10.1021/jo00307a017
- language
- English
- LU publication?
- yes
- id
- d0d052f2-a53e-41e4-b2be-5aca5ac79638
- date added to LUP
- 2021-11-11 11:54:22
- date last changed
- 2021-11-16 02:28:15
@article{d0d052f2-a53e-41e4-b2be-5aca5ac79638, abstract = {{<p>The chiral aldehydes (-)-(2<i>S</i>,5<i>S</i>)- and (-)-(2<i>S</i>,5<i>R</i>)-2-[[[dimethyl( 1,1,2-trimethylpropyl)silyl]oxy]methyl]-5-methoxy-2,5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15% yield, respectively, by lithium bromide induced rearrangement of 6-<i>O</i>-silylated methyl 2,3- and 3,4-anhydro-a- and -d-D-hexopyranosides, obtained in two steps from methyl <i>α</i>- and <i>β</i>-D-glucopyranoside. Rearrangement of various other pento- and hexoside epoxides permitted the suggestion of probable reaction routes. Hydrogenation of the unsaturated aldehydes gave the corresponding saturated aldehydes in good yield.</p>}}, author = {{Rehnberg, Nicola and Magnusson, Göran}}, issn = {{0022-3263}}, language = {{eng}}, number = {{20}}, pages = {{5467--5476}}, publisher = {{The American Chemical Society (ACS)}}, series = {{Journal of Organic Chemistry}}, title = {{Chiral Aldehydes by Ring Contraction of Pento- and Hexopyranoside Epoxides}}, url = {{http://dx.doi.org/10.1021/jo00307a017}}, doi = {{10.1021/jo00307a017}}, volume = {{55}}, year = {{1990}}, }